Bad Boy For Life: The 15 Most Gangster Moments In Puff Daddy History

by Julian Sonny

If you didn't hear by now, Diddy slapped the sh*t out of Drake in Miami over the weekend.

Of course, this wasn't a random act of violence, as it was reported that Drake was trying to scoop the hip-hop mogul's girlfriend, Cassie, while they were in the club.

But if Drake knew anything about the actual legend of Sean Combs, then surely he would've thought twice about trying to disrespect the original bad boy of the industry. Unlike Drizzy, he's actually a gangster.

If there's one thing that Diddy has proven on his epic story to the top, it's that being a nice guy gets you nowhere. He's a dick when he has to be, and occasionally, when he doesn't need to be either.

Whatever the case may be, Diddy is the man and there was no way he was going to let Drake make a Chris Brown out of him.

When he started his own record label, Bad Boy, at just 24.

After dropping out of college at Howard University, then getting fired from his first job at Uptown Records, Diddy started his own record label in 1993 called Bad Boy where he signed none other the Notorious BIG.

He would go on to see major success working with other artists, such as TLC, Mariah Carey, Boyz II Men and Jodeci. The journey he would soon after embark on would change the industry forever.

When he threatened the former president of his label with a bat to give up his share in the company.

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Former Bad Boy president Kirk Burrowes was at odds with Diddy in 1996 when he allegedly threatened his old business partner with a bat if he didn't give up his 25 percent equity in the company.

Needless to say, Diddy got his way and Burrowes bolted, despite a lawsuit being filed nearly a decade later.

When he smashed a champagne bottle over Steve Stoute's head.

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While the two are good friends today, the legend of Diddy storming into Interscope Records' executive Steve Stoute's office and smashing a bottle over his head has officially been confirmed by Stoute himself.

We got in a fight when we were kids, and it's funny that it still comes up, years later. We were millionaires at 26 years old.

According to the legend, Diddy was upset with Stoute for not editing him nailed to a cross out of Nas' "Hate Me Now" video.

He took matters into his own hands cracked a champagne bottle, which he carries around with him regularly, right over his dome.

When he beat up a rapper at the club using his cell phone.

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In a blog post by Combat Jack, a former hip-hop club goer from back in the day, he recalled Diddy as a "Gorilla Pimp" in this epic story,

Let’s take it back to Spring 1995, New York City. Bad Boy Entertainment is hip hop’s number 1 label on the East Coast and the G.O.A.T. Biggie Smalls was still alive. Jessica Rosenbaum (this Jewish chick who promotes hip hop functions) threw a weekly dinner dance event at a club called Esso’s where all the “beautiful” hip hop industry folks could gather, talk mad shit and waste ungodly amounts of money on liquor, party and bullshit. In addition to his growing record empire, Diddy was making his name as a producer and one of the many artists he produced a song for at the time (I don’t think I ever heard it) was Brooklyn rapper Positive K. K seemed like a cool dude, ran with Audio Two and MC Lyte and even scored a nationwide hit with a single called “I Gotta Man.” Anyways, I’m sitting at a table with my folks and Diddy and his weed carrying entourage make a grand entrance. Shortly thereafter, Positive K walks in dolo. Diddy sees K and approaches him. Apparently, Positive K (or, more specifically, his record label) hadn’t gotten around to paying Diddy his producer fee (which was something like 5 thousand dollars) and Diddy was heated. K looks at Diddy like “whatever nigga” and starts to walk away when Diddy whips out his cell phone (phones at the time were about the size of a brick) and starts whupping on K’s head like it was a Dora the Explorer piñata at a 6 year old’s birthday party!

When he inadvertently created bottle service while stunting with Jermaine Dupri.

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It was no question that Diddy owned the club scene during the 90s. But did you know that he and Jermaine Dupri are the ones responsible for bottle service?

According to JRose Agency and JRosenblum Events owner Jessica Rosenblum,

Puffy and Jermaine Dupri were at the bar every week—there was no such thing as bottle service. There were no ice buckets. There were no tables. They were buying out champagne at the bar, and we had to serve it to them in rubber busboy trays, because we had nothing to put champagne in. It wasn’t like now, when somebody buys a parade of Dom Pérignon or Moët Rosé, and it comes out all lovely at your table with sparklers and shit—that didn’t exist. We were literally piling up champagne in those containers busboys would go around the club and throw dirty glasses in.

When he went off on Jadakiss and Styles P on live radio.

When he dissed Tupac on Bad Boy Mixtape Vol. 4 (before he died).

When he made "Making Of The Band" contestants walk from Brooklyn to Manhattan to get him cheesecake.

In one of the most classic moments in reality TV history, Diddy punished contestants on his MTV series "Making Of The Band" by having them walk all the way to Junior's in Brooklyn to get him a slice of strawberry cheesecake, and walk all the way back to his offices in midtown Manhattan.

For those of you not familiar with the city, that is pretty damn far.

When he sonned Pharrell in "Get Him To The Greek."

When he almost fought a cop in NYC.

When Jay Z told the story about how Diddy gave him a stash of Biggie's old beats.

When he called up Charlamagne to confront him about disrespecting Cassie.

When he looked at a dollar bill like he hadn't seen one in years.

When he went back to Howard University in 1995 and brought Biggie to Yardfest.

When he went back to Howard University in 2014 and did the commencement speech at graduation.